JPH10503171A - Ｎ−（５−イソチアゾリル）アミド有害生物防除剤 - Google Patents

Ｎ−（５−イソチアゾリル）アミド有害生物防除剤

Info

Publication number: JPH10503171A
Authority: JP; Japan
Prior art keywords: alkyl; substituted; halo; phenyl; formula
Prior art date: 1994-05-17
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

JP7529898A

Other languages

English (en)

Japanese (ja)

Inventor

ロナルド・イーハクラー，

ジヨージ・ダブリユージヨンソン，

ジヤツク・ジーサマリントニ，

Original Assignee

ダウエランコ

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1994-05-17

Filing date

1995-05-17

Publication date

1998-03-24

1995-05-17 Application filed by ダウエランコ filed Critical ダウエランコ

1998-03-24 Publication of JPH10503171A publication Critical patent/JPH10503171A/ja

Status Pending legal-status Critical Current

Links

GKZNVLJEHYUFIC-UHFFFAOYSA-N 1,2-thiazol-5-amine Chemical compound NC1=CC=NS1 GKZNVLJEHYUFIC-UHFFFAOYSA-N 0.000 title abstract description 6
239000000575 pesticide Substances 0.000 title description 2
239000000203 mixture Substances 0.000 claims abstract description 86
238000000034 method Methods 0.000 claims abstract description 16
230000000895 acaricidal effect Effects 0.000 claims abstract description 13
230000000749 insecticidal effect Effects 0.000 claims abstract description 5
230000001069 nematicidal effect Effects 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims description 210
150000001875 compounds Chemical class 0.000 claims description 154
125000005843 halogen group Chemical group 0.000 claims description 142
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 126
125000003545 alkoxy group Chemical group 0.000 claims description 85
125000000753 cycloalkyl group Chemical group 0.000 claims description 46
-1 morpholino, piperidinyl Chemical group 0.000 claims description 43
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 43
125000002252 acyl group Chemical group 0.000 claims description 39
241000238631 Hexapoda Species 0.000 claims description 27
125000000392 cycloalkenyl group Chemical group 0.000 claims description 27
229920006395 saturated elastomer Polymers 0.000 claims description 25
125000003118 aryl group Chemical group 0.000 claims description 21
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 21
229910052717 sulfur Inorganic materials 0.000 claims description 17
229910052760 oxygen Inorganic materials 0.000 claims description 16
125000001183 hydrocarbyl group Chemical group 0.000 claims description 15
241000238876 Acari Species 0.000 claims description 14
229910052757 nitrogen Inorganic materials 0.000 claims description 14
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 13
125000005842 heteroatom Chemical group 0.000 claims description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 10
125000001188 haloalkyl group Chemical group 0.000 claims description 9
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 9
229930195734 saturated hydrocarbon Natural products 0.000 claims description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000004414 alkyl thio group Chemical group 0.000 claims description 7
125000000304 alkynyl group Chemical group 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
241000244206 Nematoda Species 0.000 claims description 6
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
125000004965 chloroalkyl group Chemical group 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
125000004438 haloalkoxy group Chemical group 0.000 claims description 6
125000004970 halomethyl group Chemical group 0.000 claims description 6
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
125000001544 thienyl group Chemical group 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 5
244000052769 pathogen Species 0.000 claims description 5
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
125000001246 bromo group Chemical group Br* 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
125000001041 indolyl group Chemical group 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims description 4
230000001717 pathogenic effect Effects 0.000 claims description 4
239000011591 potassium Substances 0.000 claims description 4
229910052700 potassium Inorganic materials 0.000 claims description 4
239000011734 sodium Substances 0.000 claims description 4
229910052708 sodium Inorganic materials 0.000 claims description 4
125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical class [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 3
125000006177 alkyl benzyl group Chemical group 0.000 claims description 3
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 3
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
150000001768 cations Chemical class 0.000 claims description 3
125000005046 dihydronaphthyl group Chemical group 0.000 claims description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
125000003386 piperidinyl group Chemical group 0.000 claims description 3
125000003373 pyrazinyl group Chemical group 0.000 claims description 3
125000002098 pyridazinyl group Chemical group 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
125000005505 thiomorpholino group Chemical group 0.000 claims description 3
241000239223 Arachnida Species 0.000 claims description 2
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 2
125000004849 alkoxymethyl group Chemical group 0.000 claims description 2
150000001720 carbohydrates Chemical class 0.000 claims description 2
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 4
125000001589 carboacyl group Chemical group 0.000 claims 2
125000005488 carboaryl group Chemical group 0.000 claims 1
239000000417 fungicide Substances 0.000 abstract description 12
239000002917 insecticide Substances 0.000 abstract description 10
239000000642 acaricide Substances 0.000 abstract description 9
239000005645 nematicide Substances 0.000 abstract description 7
230000000855 fungicidal effect Effects 0.000 abstract description 5
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 70
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
239000000243 solution Substances 0.000 description 39
239000000047 product Substances 0.000 description 29
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
239000000460 chlorine Substances 0.000 description 25
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 24
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
150000001412 amines Chemical class 0.000 description 19
239000003921 oil Substances 0.000 description 17
239000007787 solid Substances 0.000 description 16
241000196324 Embryophyta Species 0.000 description 15
239000002904 solvent Substances 0.000 description 15
238000010992 reflux Methods 0.000 description 14
239000000741 silica gel Substances 0.000 description 14
229910002027 silica gel Inorganic materials 0.000 description 14
238000004809 thin layer chromatography Methods 0.000 description 14
238000012360 testing method Methods 0.000 description 13
239000012267 brine Substances 0.000 description 12
230000000694 effects Effects 0.000 description 12
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 11
239000000463 material Substances 0.000 description 11
239000000284 extract Substances 0.000 description 10
238000009472 formulation Methods 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
238000004458 analytical method Methods 0.000 description 9
239000000126 substance Substances 0.000 description 9
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000012298 atmosphere Substances 0.000 description 8
239000007921 spray Substances 0.000 description 8
238000011282 treatment Methods 0.000 description 8
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
229910000041 hydrogen chloride Inorganic materials 0.000 description 7
239000012044 organic layer Substances 0.000 description 7
239000007858 starting material Substances 0.000 description 7
241000258937 Hemiptera Species 0.000 description 6
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
150000001408 amides Chemical class 0.000 description 6
239000011521 glass Substances 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
239000003960 organic solvent Substances 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
239000002253 acid Substances 0.000 description 5
238000007792 addition Methods 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
235000013601 eggs Nutrition 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
239000007788 liquid Substances 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000002002 slurry Substances 0.000 description 5
241000894007 species Species 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
241000233866 Fungi Species 0.000 description 4
241000255777 Lepidoptera Species 0.000 description 4
239000007900 aqueous suspension Substances 0.000 description 4
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QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
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238000000354 decomposition reaction Methods 0.000 description 3
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239000003995 emulsifying agent Substances 0.000 description 3
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
150000002825 nitriles Chemical class 0.000 description 3
239000012071 phase Substances 0.000 description 3
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000012085 test solution Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
229920001817 Agar Polymers 0.000 description 2
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CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
229920000742 Cotton Polymers 0.000 description 2
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RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
241001147381 Helicoverpa armigera Species 0.000 description 2
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KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
208000031888 Mycoses Diseases 0.000 description 2
ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
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238000001816 cooling Methods 0.000 description 2
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JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 description 1
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CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
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208000003643 Callosities Diseases 0.000 description 1
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241001635274 Cydia pomonella Species 0.000 description 1
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241000489975 Diabrotica Species 0.000 description 1
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IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
241001466042 Fulgoromorpha Species 0.000 description 1
206010017533 Fungal infection Diseases 0.000 description 1
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229910019142 PO4 Inorganic materials 0.000 description 1
241000233679 Peronosporaceae Species 0.000 description 1
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229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
206010037660 Pyrexia Diseases 0.000 description 1
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KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
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241000256248 Spodoptera Species 0.000 description 1
241001521235 Spodoptera eridania Species 0.000 description 1
241000256247 Spodoptera exigua Species 0.000 description 1
241001414989 Thysanoptera Species 0.000 description 1
241000255901 Tortricidae Species 0.000 description 1
241000255993 Trichoplusia ni Species 0.000 description 1
241000219094 Vitaceae Species 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
125000005431 alkyl carboxamide group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
150000001409 amidines Chemical class 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
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239000008135 aqueous vehicle Substances 0.000 description 1
235000021405 artificial diet Nutrition 0.000 description 1
229960000892 attapulgite Drugs 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
238000003763 carbonization Methods 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000001311 chemical methods and process Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
235000020971 citrus fruits Nutrition 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
229910052805 deuterium Inorganic materials 0.000 description 1
238000011161 development Methods 0.000 description 1
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
LDOIXZDCORVNPZ-UHFFFAOYSA-O diazanium bromide nitrate Chemical compound [NH4+].[NH4+].[Br-].[O-][N+]([O-])=O LDOIXZDCORVNPZ-UHFFFAOYSA-O 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000000539 dimer Substances 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
150000004662 dithiols Chemical class 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
DEQYTNZJHKPYEZ-UHFFFAOYSA-N ethyl acetate;heptane Chemical compound CCOC(C)=O.CCCCCCC DEQYTNZJHKPYEZ-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000003925 fat Substances 0.000 description 1
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235000021021 grapes Nutrition 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
238000000265 homogenisation Methods 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
230000000415 inactivating effect Effects 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
239000011872 intimate mixture Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
235000019357 lignosulphonate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
238000003801 milling Methods 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
229920001206 natural gum Polymers 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
231100000344 non-irritating Toxicity 0.000 description 1
239000012038 nucleophile Substances 0.000 description 1
235000014571 nuts Nutrition 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
235000020232 peanut Nutrition 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
235000015136 pumpkin Nutrition 0.000 description 1
239000002728 pyrethroid Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000000384 rearing effect Effects 0.000 description 1
239000011435 rock Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000007789 sealing Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000779 smoke Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
235000020354 squash Nutrition 0.000 description 1
HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000003505 terpenes Chemical class 0.000 description 1
235000007586 terpenes Nutrition 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
239000004562 water dispersible granule Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
- C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)

JP7529898A 1994-05-17 1995-05-17 Ｎ−（５−イソチアゾリル）アミド有害生物防除剤 Pending JPH10503171A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US24518494A	1994-05-17	1994-05-17
US08/245,184		1994-05-17
PCT/US1995/006307 WO1995031448A1 (fr)	1994-05-17	1995-05-17	Pesticides de n-(5-isothiazolyle)amide

Publications (1)

Publication Number	Publication Date
JPH10503171A true JPH10503171A (ja)	1998-03-24

Family

ID=22925641

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP7529898A Pending JPH10503171A (ja)	1994-05-17	1995-05-17	Ｎ−（５−イソチアゾリル）アミド有害生物防除剤

Country Status (4)

Country	Link
JP (1)	JPH10503171A (fr)
AU (1)	AU2641295A (fr)
CA (1)	CA2189573A1 (fr)
WO (1)	WO1995031448A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2002542244A (ja) *	1999-04-20	2002-12-10	シンジェンタリミテッド	殺虫性のインダゾール又はベンゾトリアゾール誘導体
WO2007077889A1 (fr) *	2005-12-27	2007-07-12	Nippon Soda Co., Ltd.	Compose benzoisothiazoline et agent d’elimination d’organismes nuisibles
WO2008007459A1 (fr) *	2006-07-12	2008-01-17	Kumiai Chemical Industry Co., Ltd.	Dérivé de 3,4-dihalogénoisothiazole et agent de régulation d'une maladie de plante agricole ou horticole
JP2009227655A (ja) *	2007-11-16	2009-10-08	Sumitomo Chemical Co Ltd	α，β−不飽和イミダート化合物およびそれを含有する有害生物防除剤
JP2010524954A (ja) *	2007-04-17	2010-07-22	アボット・ラボラトリーズ	カンナビノイド受容体リガンドとしての２−イミノイソチアゾール誘導体

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US5741818A (en)	1995-06-07	1998-04-21	University Of Saskatchewan	Semicarbazones having CNS activity and pharmaceutical preparations containing same
DE19542372A1 (de) *	1995-11-14	1997-05-15	Bayer Ag	Acylierte 5-Aminoisothiazole
DE19628569A1 (de) *	1996-07-16	1998-01-22	Bayer Ag	Substituierte N-(5-Isothiazolyl)-thioamide
DE19630814A1 (de) *	1996-07-31	1998-02-05	Bayer Ag	Substituierte N-Isothiazolyl-(thio)amide
NZ500590A (en)	1997-04-22	2001-11-30	Cocensys Inc	Carbocyclic and heterocyclic substituted semicarbazones and thiosemicarbazones and the use thereof
DE19727162A1 (de) *	1997-06-26	1999-01-07	Bayer Ag	Substituierte Aminoheterocyclylamide
DE19736545A1 (de) *	1997-08-22	1999-02-25	Bayer Ag	Acylierte 5-Aminoisothiazole
GB9816654D0 (en)	1998-07-30	1998-09-30	Zeneca Ltd	Chemical compounds
DE19846008A1 (de)	1998-10-06	2000-04-13	Bayer Ag	Phenylessigsäure-heterocyclylamide
GB9910793D0 (en) *	1999-05-10	1999-07-07	Zeneca Ltd	Chemical processes
KR20020058023A (ko) *	1999-11-18	2002-07-12	한스 루돌프 하우스, 헨리테 브룬너, 베아트리체 귄터	살충성 아미노헤테로시클릴아미드 화합물
GB0002036D0 (en) *	2000-01-28	2000-03-22	Zeneca Ltd	Chemical compounds
GB0002034D0 (en) *	2000-01-28	2000-03-22	Zeneca Ltd	Chemical compounds
PE20010830A1 (es) *	2000-01-28	2001-09-06	Syngenta Ltd	Derivados de azol insecticidas o fungicidas y composiciones que los comprenden
GB0002032D0 (en) *	2000-01-28	2000-03-22	Zeneca Ltd	Chemical compounds
GB0002029D0 (en) *	2000-01-28	2000-03-22	Zeneca Ltd	Chemical compounds
GB0002040D0 (en) *	2000-01-28	2000-03-22	Zeneca Ltd	Chemical compounds
WO2001055142A1 (fr) *	2000-01-28	2001-08-02	Syngenta Limited	Derives d'isothiazole et leur utilisation comme pesticides
GB0007245D0 (en) *	2000-03-24	2000-05-17	Zeneca Ltd	Chemical compounds
DE10015015A1 (de) *	2000-03-27	2001-10-04	Bayer Ag	Oxim-Derivate
GB0012806D0 (en) *	2000-05-25	2000-07-19	Zeneca Ltd	Chemical compounds
GB0025814D0 (en) *	2000-10-20	2000-12-06	Zeneca Ltd	Chemical processes
US6667326B1 (en)	2000-11-16	2003-12-23	Novartis Animal Health Us, Inc.	Pesticidal aminoheterocyclamide compounds
GB0102108D0 (en) *	2001-01-26	2001-03-14	Syngenta Ltd	chemical process
GB0118357D0 (en) *	2001-07-27	2001-09-19	Syngenta Ltd	Chemical compounds
JP2003238541A (ja) *	2001-12-14	2003-08-27	Bayer Ag	イソチアゾリルアミノカルボニル含有化合物及び有害生物防除剤としての利用
EP1572656B1 (fr) *	2002-12-20	2010-05-26	Dow Agrosciences LLC	Composes utilises en tant que pesticides
WO2005040143A1 (fr) *	2003-10-27	2005-05-06	Basf Aktiengesellschaft	Composes 5-(2-arylacetamido)isothiazole ii
US7241776B2 (en) *	2004-08-02	2007-07-10	Abbott Laboratories	Cyanoamidine P2X7 antagonists for the treatment of pain
JP4033409B1 (ja) *	2005-07-11	2008-01-16	田辺三菱製薬株式会社	オキシム誘導体及びその製法
WO2007140439A2 (fr)	2006-05-31	2007-12-06	Abbott Laboratories	Nouveaux composés constituant des ligands de récepteurs cannabinoïdes et utilisations de ces composés
US8841334B2 (en)	2006-05-31	2014-09-23	Abbvie Inc.	Compounds as cannabinoid receptor ligands and uses thereof
JP2010522760A (ja)	2007-03-28	2010-07-08	アボット・ラボラトリーズ	カンナビノイド受容体リガンドとしての１，３−チアゾール−２（３ｈ）−イリデン化合物
US8501794B2 (en)	2007-04-17	2013-08-06	Abbvie Inc.	Compounds as cannabinoid receptor ligands
MX2009012374A (es)	2007-05-18	2009-12-01	Abbott Lab	Compuestos novedosos como ligandos del receptor de canabinoides.
US9193713B2 (en)	2007-10-12	2015-11-24	Abbvie Inc.	Compounds as cannabinoid receptor ligands
US8846730B2 (en)	2008-09-08	2014-09-30	Abbvie Inc.	Compounds as cannabinoid receptor ligands
TW201016692A (en)	2008-09-16	2010-05-01	Abbott Lab	Novel compounds as cannabinoid receptor ligands
PA8854001A1 (es)	2008-12-16	2010-07-27	Abbott Lab	Compuestos novedosos como ligandos de receptores de canabinoides
CN106674215A (zh) *	2016-12-29	2017-05-17	新沂市中诺新材料科技有限公司	一种新型纳米级异噁唑酰胺类农药合成方法

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US4013675A (en) *	1975-05-05	1977-03-22	Ppg Industries, Inc.	N-(3-methyl-5-isothiazolyl)-2-methylpentanamide
GB1548397A (en) *	1976-06-01	1979-07-11	Lilly Industries Ltd	Acylated amino-isoxazoles and aminoisothiazoles
US4059433A (en) *	1976-06-18	1977-11-22	Fmc Corporation	3-Alkoxyisothiazole derivatives as herbicides

1995
- 1995-05-17 CA CA 2189573 patent/CA2189573A1/fr not_active Abandoned
- 1995-05-17 JP JP7529898A patent/JPH10503171A/ja active Pending
- 1995-05-17 WO PCT/US1995/006307 patent/WO1995031448A1/fr not_active Ceased
- 1995-05-17 AU AU26412/95A patent/AU2641295A/en not_active Abandoned

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2002542244A (ja) *	1999-04-20	2002-12-10	シンジェンタリミテッド	殺虫性のインダゾール又はベンゾトリアゾール誘導体
WO2007077889A1 (fr) *	2005-12-27	2007-07-12	Nippon Soda Co., Ltd.	Compose benzoisothiazoline et agent d’elimination d’organismes nuisibles
WO2008007459A1 (fr) *	2006-07-12	2008-01-17	Kumiai Chemical Industry Co., Ltd.	Dérivé de 3,4-dihalogénoisothiazole et agent de régulation d'une maladie de plante agricole ou horticole
JP2010524954A (ja) *	2007-04-17	2010-07-22	アボット・ラボラトリーズ	カンナビノイド受容体リガンドとしての２−イミノイソチアゾール誘導体
JP2009227655A (ja) *	2007-11-16	2009-10-08	Sumitomo Chemical Co Ltd	α，β−不飽和イミダート化合物およびそれを含有する有害生物防除剤

Also Published As

Publication number	Publication date
WO1995031448A1 (fr)	1995-11-23
CA2189573A1 (fr)	1995-11-23
AU2641295A (en)	1995-12-05

Publication	Publication Date	Title
JPH10503171A (ja)	1998-03-24	Ｎ−（５−イソチアゾリル）アミド有害生物防除剤
JP4610738B2 (ja)	2011-01-12	殺虫性１−（置換ピリジル）−１，２，４−トリアゾール
JP3151063B2 (ja)	2001-04-03	Ｎ−（４−ピリジル又は４−キノリニル）アリールアセトアミド殺虫剤
DE60001241T2 (de)	2003-08-28	Heterocyclisch substituierte Isoxazolidine und ihre Verwendung als Fungizide
KR101568123B1 (ko)	2015-11-11	선충류 방제용 조성물 및 방법
JP2776864B2 (ja)	1998-07-16	キナゾリン誘導体
DE60018769T2 (de)	2005-08-04	Aromatische diamid-derivate oder ihre salze, chemikalien für die landwirtschaft/den gartenbau und verfahren zu ihrer anwendung
DE3881478T2 (de)	1993-09-16	Substituierte carbonsaeure-derivate, verfahren zu ihrer herstellung und diese enthaltende fungizide fuer acker- und gartenbau.
JP5437411B2 (ja)	2014-03-12	２−（３，５−二置換−４−ピリジル）−４−（チエニル、チアゾリルまたはアリールフェニル）−１，３−オキサゾリン化合物
JP2000516260A (ja)	2000-12-05	有害生物防除性３―（置換フェニル）―５―（チエニルまたはフリル）―１，２，４―トリアゾール
JPH09507245A (ja)	1997-07-22	Ｎ−（４−ピリミジニル）アミド有害生物防除剤
JP4864269B2 (ja)	2012-02-01	農薬としての３−チオメチルピラゾール
JP4763195B2 (ja)	2011-08-31	農薬としてのテトラヒドロピリジン
JP2767241B2 (ja)	1998-06-18	殺虫性のｎ−（場合により置換された）−ｎ′−置換−ｎ，ｎ′−ジ置換ヒドラジン
JPH04225965A (ja)	1992-08-14	殺虫活性を有するバルビツール酸誘導体、その製造方法および該バルビツール酸誘導体を有効成分とする殺虫剤組成物
CN118754821B (zh)	2025-06-24	一种间二酰胺类化合物及其作为农药可接受的盐、制备方法、组合物和应用
JP2004521130A (ja)	2004-07-15	Ｎ−置換テトラヒドロピリヂン及びそれらの農薬としての使用
JP4677100B2 (ja)	2011-04-27	３−（置換フェニル）−５−（置換シクロプロピル）−１，２，４−トリアゾール化合物
JP2001519796A (ja)	2001-10-23	芳香族アミド、その製造方法及び農薬としてのその使用
JPH09176170A (ja)	1997-07-08	殺微生物剤
JPH0368566A (ja)	1991-03-25	５‐置換３‐アリールインオキサゾール‐誘導体、その製法及びこれを含有する有害生物防除剤
CN113347883A (zh)	2021-09-03	杀有害生物组合物和方法
CN113194721A (zh)	2021-07-30	杀有害生物组合物和方法
JPH05286970A (ja)	1993-11-02	２−アシルアミノ−２−チアゾリン化合物、その製法及び有害生物防除剤
WO2026061411A1 (fr)	2026-03-26	Composé de pipéridine et son procédé de préparation, composition et utilisation associées

JPH10503171A - Ｎ−（５−イソチアゾリル）アミド有害生物防除剤 - Google Patents

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